1923-01-9

Usage

Uses

Used in Organic Synthesis:
Trimethyl-(1-phenylethenyl)silane is utilized as a reagent in organic synthesis for its ability to introduce silane groups into target molecules, enhancing the reactivity and properties of the synthesized compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trimethyl-(1-phenylethenyl)silane is employed as a precursor for the development of functionalized silicon compounds that can be incorporated into drug molecules, potentially improving their efficacy, stability, and delivery.
Used in Material Science:
Trimethyl-(1-phenylethenyl)silane is used as a precursor in the synthesis of silicon-containing materials, such as polymers and coatings, which can exhibit unique properties like thermal stability, resistance to environmental degradation, and enhanced performance in various applications.
Used in Chemical Research:
In the realm of chemical research, trimethyl-(1-phenylethenyl)silane serves as a valuable tool for studying the reactivity and properties of silicon-containing compounds, contributing to the advancement of silicon chemistry and its applications in various fields.

InChI:InChI=1/C11H16Si/c1-10(12(2,3)4)11-8-6-5-7-9-11/h5-9H,1H2,2-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 618-34-8 1-chlorostyrene 
• 98-81-7 1-bromovinylbenzene 
• 56975-77-0 N'?(1?phenylethylidene)benzenesulfonohydrazide 
• 5908-41-8 benzoyltrimethylsilane 
• 917-64-6 methyl magnesium iodide 
• 13411-45-5 trimethyl(2-phenyl-1,3-dithian-2-yl)silane 
• 50-00-0 formaldehyd 
• 87729-79-1 C₁₉H₂₈SSi₂ 
• 67300-99-6 1-phenylethenylmagnesium bromide 
• 591-50-4 iodobenzene 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 38111-44-3 phenylzinc(II) bromide 
• 63935-93-3 benzoyltriethylsilane 

Downstream Products

• 29113-64-2 ethyl 2-methyl-5-phenylfuran-3-carboxylate 
• 133942-56-0 2-Methyl-5-phenyl-furan-3-carboxylic acid isopropyl ester 
• 133942-55-9 2-Methyl-5-phenyl-5-trimethylsilanyl-4,5-dihydro-furan-3-carboxylic acid isopropyl ester 
• 942-92-7 caprophenone 
• 35153-45-8 ethyl 3-(phenyl-3-trimethylsilyl)propionate 
• 100-42-5 styrene 
• 109573-66-2 ((1R,2S)-1,2-Bis-trimethylsilanyl-cyclopropyl)-benzene 
• 124306-23-6 Z-1-chloro-2-phenyl-2-trimethylsilyl-cyclopropyl phenyl sulfide 
• 98-83-9 isopropenylbenzene 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 4714-21-0 E-1-methyl-4-styryl-benzene 
• 1694-20-8 trans-4-nitrostilbene 
• 6624-53-9 (Z)-1-nitro-4-(2-phenylethenyl)-benzene 

Relevant academic research and scientific papers

1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C 2 Building Block

1-(Trimethylsilyl)vinyl MIDA boronate - a trifunctional C 2 building block - is prepared in only two laboratory steps and 54% overall yield starting from readily available trimethyl(vinyl)silane. The title compound undergoes orthogonal functionalization at either of the groups present in its structure, for example, iodination at the trimethylsilyl moiety, epoxidation at the double bond, and Suzuki-Miyaura coupling at the MIDA boronate.

Preparation of Functionalized Acylsilanes by Diol Cleavage of Cyclic 1,2-Dihydroxysilanes

We report a study on diol cleavage of cyclic 1,2-dihydroxysilanes for the preparation of functionalized acylsilanes. Sodium periodate turned out to be an efficient reagent for this transformation, resulting in good to excellent yields. The method is chara

Styrylsilane coupling reagents for immobilization of organic functional groups on silica and glass surfaces

Styrylsilanes serve as new coupling reagents for introducing organic functional groups on silica and glass surfaces. Functionalized styrylsilanes, which are readily prepared via catalytic hydrosilylation of the corresponding phenylacetylenes with silanes, are immobilized on silica through acid catalyzed processes under mild conditions.

Preparation of Optically Active cis-Cyclopropane Carboxylates: Cyclopropanation of α-Silyl Stryenes with Aryldiazoacetates and Desilylation of the Resulting Silyl Cyclopropanes

Optically active cis-cyclopropane carboxylates are prepared via the Rh2(S-PTAD)4-catalyzed cyclopropanation of α-silyl styrenes with aryl diazoacetates followed by desilylation of the resulting silyl cyclopropane carboxylates. The co

Mg-promoted reductive coupling of aromatic carbonyl compounds with trimethylsilyl chloride and bis(chlorodimethylsilyl) compounds

Mg-promoted reductive coupling of aromatic carbonyl compounds (1) with chlorosilanes, such as trimethylsilyl chloride (TMSCl:2), 1,2- bis(chlorodimethylsilyl)ethane (3) and 1,5-dichlorohexamethyltrisiloxane (4), in N,N-dimethylformamide (DMF) at room temperature brought about selective and facile reductive formation of both of carbon-silicon and oxygen-silicon bonds to give the corresponding α-trimethylsilylalkyl trimethylsilyl ethers (5) and cyclic siloxanes (6), (7) in moderate to good yields, respectively. The present facile and selective coupling may be initiated through electron transfer from Mg metal to aromatic carbonyl compounds (1).

A new silicon-mediated elimination-rearrangement

Treatment of trimethylsilylethanes bearing α-phenyl groups and β-phenylthio, phenylsulfonyl or cyano groups with LDA causes elimination-rearrangement mediated by the β-carbanionic species. Mechanistic conclusions are based on isotopic labelling experiment

Mg-promoted reductive cross coupling of carbonyl compounds with trimethylsilyl chloride

Mg-promoted cross-coupling of aromatic carbonyl compounds with trimethylsilyl chloride (TMSCl) in DMF at room temperature brought about reductive carbon-silicon bond formation to give the corresponding α-trimethylsilylalkyl trimethylsilyl ethers selectively in good yields.The reaction may be initiated through electron transfer from Mg metal to the carbonyl compounds.

Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

Trimethylsilylmethyl ketones, readily available from acyl chlorides, undergo a Reformatsky-Peterson reaction sequence to give 3-alkenoates regioselectively.Acylsilanes, however, react with either zinc ester enolates or trimethylsilylmethylmagnesium chloride to give the corresponding tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement-Peterson olefination sequence.These reactions allow the selective formation of vinylsilanes.

Synthesis of 3-substituted furans by directed lithiation and palladium catalysed coupling

The 5-position of the furan ring of 4,4-dimethyl-2-(2-furyl)oxazoline (1a) was protected by a trimethylsityl group. The product, compound (2a), was then lithiated at the 3-position with sec-butyllithium and converted to the bromozinc species (2d) with zinc bromide. Coupling reactions with a range cf aryl-, acyl-, and vinyl halides were performed with Pd(PPh3)4 as catalyst. The reaction with (1-bromoethenyl)- trimethylsilane is abnormal in that it gives a mixture of two products (21) and (2m). The origin of the abnormal product (21) is discussed. The coupling reactions of this silane with 2-thienyl-, 2-furyl-, and phenyl-zinc bromide have also been carried out: in each case, a mixture of the expected coupling product and an isomer, the ethen-2-yltrimethylsilane, was obtained. The ratio of products is shown to depend upon the temperature at which the coupling is carried out. 4,4-Dimethyl-2-(2-thienyl)oxazoline (1b) was lithiated at the 3-position of the thiophene ring and coupled to iodobenzene without protection of the 5-position.